Ethanol → HCID 23513428, compound

HRID 1741539Notes

Reaction equation

HRID 1741539 reaction equation
C(O)C.C[O-].[Na+].[C:7]([O:12]CC)(=O)[CH:8]([CH3:10])[OH:9].[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([CH3:23])=[CH:20][C:21]=1[OH:22]>CO.C(Cl)(Cl)Cl.O>[OH:22][C:21]1[CH:20]=[C:19]([CH3:23])[CH:18]=[CH:17][C:16]=1[NH:15][C:7](=[O:12])[CH:8]([OH:9])[CH3:10]

Participants

7

Reactant 4

HCID 702EthanolHCID 7344Ethyl LactateHCID 760822-Amino-5-methylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 23513428HCID 23513428, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21584188Chloroform methanolSolvent

Procedure

To 20 ml of ethanol, there were added 6.72 g of sodium methoxide, 20.0 g (169 mmol) of ethyl lactate and 6.95 g (56.5 mmol) of 6-amino-m-cresol, followed by heating under reflux for 3 hours. After cooling, 100 ml of water was added to the mixture and the crystals thus precipitated were filtered. The filtrate was extracted with 200 ml of ethyl acetate, washed with a saturated aqueous solution of common salt and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, the solid thus obtained was subjected to silica gel column chromatography (Si60 manufactured by Merck; 230-400 mesh; 300 g; eluent: 2% methanol-chloroform). After distilling off the solvent from the 2,000-3,200 ml fraction under reduced pressure, the obtained solid was dissolved in 200 ml of ethyl acetate, washed with 1N hydrochloric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and dried over anhydrous Glauber's salt. After distilling off the solvent under reduced pressure, the residue was dried and thus 0.70 g (3.6 mmol) of N-(2-hydroxy-4-methylphenyl)-2-hydroxypropionamide was obtained as brown crystals. The yield was 6%.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe crystals thus precipitated
  5. filtrationwere filtered
  6. extractionThe filtrate was extracted with 200 ml of ethyl acetate
  7. washwashed with a saturated aqueous solution of common salt
  8. dry with materialdried over anhydrous Glauber's salt
  9. distillationAfter distilling off the solvent under reduced pressure
  10. customthe solid thus obtained
  11. distillationAfter distilling off the solvent from the 2,000-3,200 ml fraction under reduced pressure
  12. dissolutionthe obtained solid was dissolved in 200 ml of ethyl acetate
  13. washwashed with 1N hydrochloric acid
  14. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of common salt and dried over anhydrous Glauber's salt
  15. distillationAfter distilling off the solvent under reduced pressure
  16. customthe residue was dried

Sources & evidence

ORD record
ord-80c34c34d0d14cdd9cdc49edcfe448c6
Source dataset
uspto-grants-1994_08
Patent number
US05334225

Reaction notes

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